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Claude
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I do a lot of repeat work: weekly reports, client updates, rewriting product descriptions. Right now I keep everything in one giant chat because I'm scared of losing the context.

Is that a bad idea? When does it make sense to start fresh, and what's the cleanest way to carry over what Claude already knows about my work?

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It's not a bad instinct to want to keep context, but one giant chat usually works against you. Long chats get slower to steer, and earlier instructions get diluted (see the question about Claude forgetting instructions).

A simple way to decide:

  • New task, new chat. A weekly report and a product description have nothing to do with each other, so they shouldn't share a chat.
  • Same task, same chat. Keep going while you're refining one piece of work.
  • Repeated work gets a saved starting point. Write down the things Claude should always know about your work (your role, your clients, your tone, the format of the report) and paste them at the start of each new chat, or keep them in a Project so they're there every time.

That way you lose nothing, because the context lives in your saved notes and not in a chat you're afraid to close.

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